


All's Well That Ends Well

by caffeinechesters



Category: Supernatural
Genre: Bottom Sam, Hair-pulling, M/M, set vaguely in season 1
Language: English
Status: Completed
Published: 2018-06-01
Updated: 2018-06-01
Packaged: 2019-05-16 17:22:34
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,669
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14815619
Author URL: https://archiveofourown.org/users/caffeinechesters/pseuds/caffeinechesters
Summary: Dean shouldn't get jealous if he can't tell Sam that he wants him.





	All's Well That Ends Well

**Author's Note:**

> I had the option to choose between hair-pulling or the use of sex toys for my challenge. My muse said "Why not both?"
> 
> Also, the title is straight up from Shakespeare.

It shouldn’t have surprised Dean as much as it did when found out. He knew Sam was proud of his hair, even if he never said it. Now that he knew that Sam liked his hair pulled during sex, he can’t get it out of his head. Sure he and Sam fucked out as teens, but now that he’s back from Stanford, they have both stayed mum about it.

Dean realizes in hindsight he probably should’ve just waited until Sam was done in the bar’s bathroom to go in. Especially after seeing Sam being followed in by a dude that was bigger than him, maybe not in height, but definitely more bulky muscle compared to Sam’s whipcord muscle. He was just being an awesome big brother. He was just making sure that the guy wasn’t going to bash Sam’s skull for hustling him at pool. He wasn’t expecting to see Sam on his knees sucking this barfly’s dick. He definitely didn’t need to hear the moan Sam made when his hair was pulled by the guy, his hair being used to guide him on his dick. Dean may not be a coward when it comes to monsters, but seeing your baby brother on his knees for a random stranger and finding out he gets all hot and bothered by getting his hair pulled, he retreated back to the booth to wait for Sam to finish.

That was two states ago and a hunt ago. Dean isn’t ashamed to admit that he’s jerked off to that night; that it’s him that Sam is blowing and it’s his fist that is knotted up in Sam’s hair. He wants to ask Sam about it, the hair pulling and a blowjob if he isn’t lying to himself. He doesn’t know how to approach it. He imagines that Sam might give him an epic bitch face if he asks for it and tell him he’s being crude or worst that he regrets what they did before Stanford. Sam hasn’t given any indication if that he remembers all the hours they logged into motel beds or the backseat of the impala. He’s seen Sam give him the looks like he did as a teen, but never moves past that. Dean thinks he outwait Sam. He can be patient.

He feels his patience weaning when looking for a clean pair of socks in Sam’s duffel he comes across a butt plug, a dildo, and a bottle of lube (that looks like semen he notes) buried underneath dirty socks and underwear. He quickly places everything back in order before Sam gets out of the shower. He never knew Sam liked sex toys. He needed to stop thinking about Sam and sex toys. Well, for now. Now they have to go interview a witness.

They caught a week without any monsters. Well, there’s always monsters, but it was quiet on the monster front. Dean goes out to the dive bar near the motel they’re crashing it. Sam tells him that he wants “research and look for new hunts”, which Dean is okay with. He won’t feel Sam giving him bitch faces when he tries to pick up people, especially the bartender. As it turns out, a couple of hour in and a couple of beers and a few shots of whiskey later, there is no one here that he would want to be caught dead in bed with. He finishes is last beer and decides to cut his losses and head back to the room. Sam is probably sleeping, so he opts to be come in quietly. Because Dean is a nice big brother like that. What he wasn’t expecting was walking into the room and seeing Sam on his hands and knees fucking himself with a dildo. An impressively sized dildo. With lube dripping out him making it look like someone else fucked him. He shouldn’t feel jealous over a dildo (he does). If he was a better person, he would quietly leave and come back later. Much later. Instead, he watches, like a creep. Dean isn’t sure where he could be watching: the dildo Sam keeps corkscrewing, fucking himself with or the way his dick is just leaking precome. Which, Dean can relate to in this moment, feeling his dick getting wet and throbbing to be the one buried in Sam. Seriously, he’s not jealous of the dildo. Much. It all comes crashing down when he gets a hand around his dick and he lets out a loud moan. The wet, squelching sound coming from the bed stops. Sam is grinning. Dean knows he’s been caught with his hand in his pants, both literally and proverbially.

“Enjoying the show, Dean,” Sam asks, looking every bit of the cat that ate the canary as he starts to pull out the dildo and push it back in again.

Dean is dumbfounded. Dean just manages a raspy “ Yeah Sammy.”

Sam grins. Dean will always love Sam, but right now, he’s never been more in love, especially when he hears Sam tell him, “Come on Dean. Show me how much you changed since the last time.”

And Dean’s war with patience is over. He strips as he walks over to the bed. He spreads Sam open wide, watching the way his brother’s hole just takes the dildo. He runs a finger along his rim, feeling how wet Sam is and give around his finger, letting it slip in just a little. Sam moans, his thighs trembling when Dean hooks his finger, aiming for his prostate.

“Dean, Dean,” Sam moans, “Fuck me please.”

“It looks like you’re fucking yourself good enough,” Dean quips pulling out his finger to insert another one along side it.

Before he get a change to do that, he sees Sam removing the dildo. He sees the nice gape he has, and Dean is weak. He feels his resolve disappear when Sam clenches and not quite closing. The puffy, red rim and lube slick shine is the last straw for Dean to grab the lube beside Sam, slick himself up, and press the head of his dick to his hole. He rubs the head along Sam’s rim before pressing in. He stops once the head of his dick is in. He feels like he’s about to come quicker than his first time under the bleachers with a cheerleader. Dean needs a moment. It’s the first time they’ve had sex since before Sam left. He wants to make it good. He wants it to last. Sam, ever such the bitch, decides for the both of them as he pushes back against Dean until Sam’s ass is flushed against his hip bones. Dean groans. If he was into chick flick moments, he’d tell Sam that he missed him more than he will ever know while at Stanford and not just because of the sex. Instead, he goes straight into the dirty talk.

“Yeah, Sammy, just like that. Your ass is the best thing that my dick as been in,” Dean mumbles as he starts to thrust. “And I know a little kink you have. Found out when you were sucking off some dick in a bar bathroom.”

He fists a hand into Sam’s hair and pulls slightly. He feels Sam clench down as he moans. God, he missed how Sam’s dime word vocabulary disappears when he was getting fucked. Dean makes sure to set a counter-rhythm to his thrusts when tugs at Sam’s hair, carefully. He doesn’t want to Sam to have a bitch fit when he comes to and realizes that Dean pulled out some of his precious locks. 

Dean gets lost in the feeling of Sam, the little “ah, ah, ahs” when he tugs a bit too hard, and the wet, squelching sound of too much lube coupled with the squeaks of an old motel mattress. Dean thinks this is what his heaven will be if he goes there: Sam, an old motel room, and unlimited lube and sex toys.

He can tell Sam is getting closer, his thighs are trembling more and the only reason his head isn’t slumped down between his shoulders is because of Dean’s grip. He decides to up the ante. Dean grips Sam’s hair tighter, moving the his hand that was on his hip to his lower stomach, and pulls Sam into his lap and pushes his dick into Sam as deep as he can go. That is when he feels Sam lose it, coming all over himself and Dean’s hand his stomach. Dean follows soon after, small thrusts trying to get deeper.

Dean lays Sam down and watches in fascination when he pulls his dick out. Sam’s hole is even more gaped before, a mess of lube and come and Dean thinks maybe a little turned out. He feels his dick trying to go for a second around. Sam makes a disapproving noise as Dean thumbs around his hole as if he knew what Dean was thinking. He should get Sam cleaned up. He stands up before his dick overrides his brain. 

He goes to the bathroom to get a warm washcloth and heads back to the bed to see Sam stretched out. Dean thinks back to the first time and smirks about how if only younger him knew that Sam was a kinky bastard. He tosses the washcloth on the small of Sam’s back, resulting in a wet smack sound and Sam looking over his shoulder with a bitchy look. He may love Sam more than he loves himself, but he’s still the older brother. He can’t go soft on Sam when it comes to pranks and one-upmanship. Dean after having a little laugh, carefully cleans him up, making sure that he didn’t tear. Sam just melts under the care. He pulls the blanket from the other bed, curls up beside Sam, and covers them both up.

As Dean is about to drift off, he hears Sam say “It took you long enough to realize that I wanted this again.”


End file.
